Lithium Hydroxide → HCID 59708794, compound

HRID 1097300Notes

Reaction equation

HRID 1097300 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:11][CH2:10]1)C.C1COCC1.[OH-].[Li+]>CO.O>[C:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3])[CH2:14][CH2:13]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59708792HCID 59708792, compound

Product 1

HCID 59708794HCID 59708794, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 5-[4-(4-tert-butoxycarbonylaminobutyl)piperazin-1-yl]pentanoic acid ethyl ester (18) (1.62 g, 4.20 mmol) in methanol (12 mL)/THF (10 mL) was added a solution of lithium hydroxide (0.35 g, 8.40 mmol) in water (4 mL). The reaction mixture was stirred at room temperature for 20 h and then concentrated in vacuo. The resulting residue was diluted with water (5 mL) and acidified to pH ˜5 with 1 N aqueous HCl. The aqueous solution was extracted with chloroform/2-propanol (3:1, 3×10 mL). The combined extracts were concentrated under vacuum to dryness. The resulting residue was further co-evaporated with toluene and dried under high vacuum to give the desired acid 19 as a colorless, thick oil (1.42 g, 95%): 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.63 (m, 8H), 2.30 (m, 2H), 2.58 (m, 2H), 2.68 (m, 2H), 2.92 (m, 8H), 3.12 (m, 2H), 4.92 (br, 1H); ESI MS m/z 358 [C18H35N3O4+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe resulting residue was diluted with water (5 mL)
  3. extractionThe aqueous solution was extracted with chloroform/2-propanol (3:1, 3×10 mL)
  4. concentrationThe combined extracts were concentrated under vacuum to dryness
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b92d793bbfc34589a08c8f62e56573b1
Source dataset
uspto-grants-2012_03
Patent number
US08143256B2

Reaction notes

Loading…